Email Deliverability: Hotmail

Dec 1, 2025 - 5:57 AM

https://megagrass.com/community/question-and-answer/forums/4133/topics/2982892 COPY
  • Hi all. Has anyone heard how Square is handling deliverability? I assume we are all on shared IPs which I know innately is difficult as that means whatever others are doing wrong in email will hurt the group. However, in the last 2 weeks I am seeing all Microsoft (microsoft, hotmail, outlook, msn) email addresses are bouncing. Customers that had been receiving emails are no longer getting them, including our cheese club members. Have others noticed this and is there anything Square is doing to fix it?

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  • I don't know how to check our DNS settings with Square, if anyone knows how to do that I would like to see if msft has it blacklisted.

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  • I had the same issue a while back and it turned out the emails were getting flagged because of a poor sender reputation. I ran an ip blacklist check https://www.inboxally.com/spam-database-lookup on the sending domain just to be sure and found it was showing up on a couple of lists. Once that was cleared and I adjusted some DNS records, things started working again. Might be worth checking your IP status too.

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  • Email deliverability to Hotmail can be tricky with their strict filters. I tackled this by running every address through MailTester.Ninja my ultimate bounce killer that verifies emails and keeps my sender reputation clean even with Hotmail domains. This email checker and finder cuts bounce rate by 98% and supercharges every campaign. Once deliverability is sorted, I take a well-deserved break offline. Practical topic, glad this forum covers it.

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